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CHICAGO WHITE SOX
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Signed SS-R Tim Anderson to a six-year, $25 million contract extension. [3/21]

This kind of contract is the team-betting-on-performance extension. Granted, there aren’t too many deals quite like this one these days—the White Sox’s young shortstop is signing this deal despite not reaching free agency until 2023—but teams like the Rays and Astros have been looking to lock down even the youngest of their potential stars for years. Signing a yet unproven pre-arbitration player to a move like this where free agency gets delayed at the club’s option gives a franchise both cost certainty and amazing value if the player’s performance blows up.

Anderson, a former top prospect who fared moderately well in his first taste of the majors, represents a smart investment as the White Sox look to build for the future. His true breakout potential could depend entirely on the answer to one simple question: can he get on base enough? The fleet shortstop has athleticism for weeks and enough power and hit tool to make one stand up and notice, but he walked just 13 times in 431 plate appearances. Former White Sox slugger Adam Dunn would be rolling over in his grave, were he dead.

Until we find out if Anderson will have the empty batting average of too many past White Sox shortstops, it’s hard to project him as anything more than a decent seat-filler at short whose defensive and on-base shortcomings prevent him from being an above-average regular. However, the upside here is quite high; in the event he can wrangle an on-base percentage substantially north of .300, he could quickly become one of the many franchise-cornerstone shortstops in a league that’s positively lousy with stars at the six.

PECOTA is trying to predict the future along with the White Sox and they see a near-average regular at the 50th-percentile mark, but the margin for error in both directions on Anderson is high. He could be a star or he could be another example of a player whose approach issues make him nigh-unplayable and stunt his ability to develop all his other nascent skills. For that reason, Anderson taking a relatively small payout—at least compared to his arb numbers if he starts contending for a batting title—today in case the future isn’t so bright … well, it certainly makes some sense.

This feels like one of those deals where one of the two sides is going to be disappointed three seasons in; either the White Sox are going to be bummed out that he’s still an offensive cipher or Anderson’s going to wish he’d made a larger bet on his own prodigious talents. Sure, the third path—where he’s about a one-win shortstop for the next six years—splits the difference nicely, but like many of Anderson’s at-bats, this deal could be boom-or-bust.

TAMPA BAY RAYS
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Signed CF-L Kevin Kiermaier to a six-year, $53.5 million contract extension. [3/20]

Kiermaier's extension seems a compromise struck as part of an equitable partnership. With two Gold Gloves, a Platinum Glove, and a 17th-place MVP finish, Kiermaier might have enough accolades and repute to score a substantial arbitration salary, even before he was due to hit free agency. No, there was no chance that he’d earn an amount commensurate with his overall value or WARP numbers—arbitrators are still notorious in their reliance on old-school metrics—but the Barry Bonds of outfield defense was going to make some money soon.

This deal seems more like a player trying to maximize his profits and a team trying to maximize on-field value more like your average free-agent signing. I just never expected the stingy Rays to go this route. If you look back on the history of big contracts given out by Tampa Bay, they are almost always extensions offered to young players whom they’ve developed. Ben Zobrist, Evan Longoria, Matt Moore, Chris Archer, and now Kiermaier. Though the Rays are notoriously thrifty spenders, when the front office thinks they’ve identified an extraordinary talent they seem more than willing to spend to retain them.

And though this young outfielder doesn’t have the traditional stat lines of an All-Star outfielder, the Picasso of Defense has earned approximately 3.5 WARP per season despite a few nagging injuries and FRAA’s lower-than-the-consensus view of his defense. No outfielder in baseball makes more plays that Kiermaier, who turns a double into an out nearly once per game. His defense is the fulcrum on which the Rays’ run prevention strategies turn, he’s a well-above-average baserunner, and he’s a decent enough hitter to not embarrass himself at the plate. Heck, he even amped up his walk rate last season to give his OBP a boost.

Still, entering his age-27 season and without prospect pedigree or outstanding offensive tools, he’s probably not the type of player to make a big splash in arbitration or free agency. Like so many Rays in history, he’s an undervalued asset. I never expected Tampa Bay to make this sort of move, given how they have been forced to make baseball decisions with cash in mind. Kiermaier is the game’s most elite outfield defender, but the acquisition of Mallex Smith earlier this offseason allowed us to imagine a world in which the Rays moved on from Kiermaier and attempted to find a slightly worse, significantly cheaper alternative.

Like Kiermaier, Smith is a defense-first outfielder who could eventually find a way to be an outstanding gloveman in center. But Smith is a “could” while Kiermaier is an “is.” So instead, Tampa Bay has invested deeply—for them at least—in a player whose value far outstrips his contract thanks to an oddball collection of talents. A borderline All-Star who has an undervalued skill set? An extension that makes him an integral part of the team going forward, but giving him the chance for one more big payday in his early 30s? If you can look past the fact that he doesn’t have positional flexibility and isn’t an on-base machine, maybe the Rays have found their “next Ben Zobrist.”

ST. LOUIS CARDINALS
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Signed RHP Carlos Martinez to a five-year, $51 million contract extension. [2/2]

It has been about a month and a half since the Cardinals and Martinez came to an agreement on this extension, and in that time Martinez has stayed healthy. This is excellent news for both team and player, and for every lunar crossing that goes by without a blown ligament this deal will look more and more team-friendly. This extension is prototypical in one way: it’s your standard-issue insurance contract that a pitcher takes out on himself, assuring a medium-sized payday, even if there’s an injury, in exchange for the upside of earlier free agency.

But I’ll argue that it’s irregular in another: the man they call “Tsunami” has remarkably low downside risk in the event he stays healthy, making this deal almost entirely about injury, as opposed to the combination of health and performance risk. Carlos Martinez is that good. After years as a top prospect and two partial-season stints as an exciting-but-erratic reliever, Martinez has ripped off 60 strong starts over two years, establishing himself as the type of young front-end starter front offices drool over. Top-end velocity? Check. Swing-and-miss stuff? Check. A worm-burning heater that gives him another way to get out of jams? Check.

And he’s also 25 with room to grow into his breaking stuff and refine his command. No, he doesn’t have the raw filth of a Syndergaard or a Strasburg, but Martinez has settled nicely into the role of staff ace with a Cardinals team in desperate need of his presence. The only thing that appears to be able to slow this force of nature is injury, and after a post-215 shoulder scare it seems reasonable that this bird would look to hedge some of his bets against the spectre of a wounded wing. If you look at his rotation mates—Alex Reyes just went down with a torn UCL, Lance Lynn is recovering from the same, Michael Wacha is a shell of his 2013 self—it’s easy to see why even such a strong candidate for continued stellar performance might offer up a couple of free agent years at a below-market price.

Ten-million dollars per season is fine for the steady-but-homer-prone vet you pick up at 32 years old in free agency, for Martinez it looks like grand larceny for every season he pitches remotely as well as he has up to this point. Hell, teams would and should pay $51 million for just two seasons of this type of no. 2 starter. But as we all know, we can’t trust the future and we certainly can’t trust our connective tissue. When your franchise is lucky or good enough to develop an asset like Martinez, sometimes you can turn an inexpensive young asset that’s paid pennies on the dollar into a slightly-more-expensive young asset that’s paid dimes on the dollar.

You take your extra couple of years of control and your bonus option years and say, “Thank you very much.” Sure, there is risk in a deal like this, and no one was forcing the Cardinals to pay over-arb figures for these next few years, but St. Louis is still getting top-end production here for a lovely price. And while things could change for Martinez, the security that comes from a deal like this should keep him smiling in Cardinal red for the foreseeable future.